N-叔丁氧羰基-2,5-二氢吡咯-3-羧酸乙酯 | 146257-00-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: N-叔丁氧羰基-2,5-二氢吡咯-3-羧酸乙酯
• 英文名称: N-t-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: N-t-butyloxcarbonyl-2,5-dihydro-1H-pyrrole-3-ethylformate；1-(tert-butyl) 3-ethyl 2,5-dihydro-1H-pyrrole-1,3-dicarboxylate；2,5-Dihydro-pyrrole-1,3-dicarboxylic acid 1-tert-butylester 3-ethyl ester；Ethyl N-Boc-2,5-dihydropyrrole-3-carboxylate；1-O-tert-butyl 3-O-ethyl 2,5-dihydropyrrole-1,3-dicarboxylate
• CAS: 146257-00-3
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: HOOXYTICVUYNKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-tert-Butyl 3-ethyl 1H-pyrrole-1,3(2H,5H)-dicarboxylate
Synonyms: Ethyl N-Boc-2,5-dihydropyrrole-3-carboxylate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 1-tert-Butyl 3-ethyl 1H-pyrrole-1,3(2H,5H)-dicarboxylate
CAS number: 146257-00-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H19NO4
Molecular weight: 241.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-2,5-二氢吡咯-3-羧酸乙酯 在 哌啶 、 水 、 sodium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-((4-cyanobenzene)sulfonyl)-N-hydroxy-2,5-dihydro-1H-pyrrole-3-formamide
  参考文献：
  名称：

  PYRROLIC AMIDE COMPOUND AND PREPARATION METHOD AND APPLICATION THEREOF

  摘要：

  本发明公开了一种吡咯酮酰胺化合物，如公式I所示，或其晶型形式，以及药学上可接受的盐、水合物或溶剂合物，其中R1从氢、羟基、氰基、卤素、羧基、C1-C6烷基等中选择；R2从氢、羟基、氰基、卤素等中选择；R3从羟基等中选择；X从群中选择，m等于0、1、2或3，n等于0、1或2。本发明提供的公式I所示的新化合物具有高脱乙酰酶抑制活性；同时，本发明中用于制备新化合物的方法具有步骤少、操作简单方便、安全、环保、产率高等优点，非常适合工业应用。

  公开号：

  US20170298016A1
• 作为产物：
  描述：

  N-BOC-4-氧代-3-吡咯烷甲酸乙酯 在 盐酸 、 sodium cyanoborohydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 N-叔丁氧羰基-2,5-二氢吡咯-3-羧酸乙酯
  参考文献：
  名称：

  含吡咯烷残基的短 β-肽在水溶液中形成 12-螺旋

  摘要：

  近年来，具有明确定义和可预测构象的低聚物（“折叠体”）已成为广泛关注的主题。1,2 折叠策略可用于创建特定的分子形状或功能组的特定排列，这是许多设计目标所要求的。控制形状和表面功能的传统方法涉及通常是非周期性的小型刚性骨架。相比之下，低聚物显示出高主链周期性，侧链产生官能团多样性。相对于传统支架，低聚支架的使用可以证明是有利的，因为周期性结构没有固有的尺寸限制，并且因为骨架周期性和侧链变异的组合有利于通过组合变异和选择的循环来优化分子特性。然而，大多数已知的寡聚体在构象上具有很强的流动性，至少在较短的时候（<10 个残基），这种灵活性在许多设计目标的背景下是不利的。我们描述了一组 α-氨基酸寡聚体（“α-肽”1,3），它们在水溶液中采用特定的螺旋构象，只有四个残基。水溶液中的构象稳定性对于生物学应用很重要。在常规肽（R-氨基酸残基）中，在水中的构象稳定性通常低于其他常见溶剂。4 在水溶液中检测到的非天然折叠物相对较少，5

  DOI：

  10.1021/ja000093k

文献信息

• Iridium-Catalyzed Enantioselective Hydrogenation of Unsaturated Heterocyclic Acids
  作者：Song Song、Shou-Fei Zhu、Liu-Yang Pu、Qi-Lin Zhou

  DOI：10.1002/anie.201301341

  日期：2013.6.3

  binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF−=tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate, Boc=tert‐butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities.

  螺旋结合：一种高度对映选择性的不饱和杂环羧酸的加氢已经通过使用手性铱/ spirophosphino恶唑啉催化剂开发（参见方案; BAR ˚F - =四[3,5-双（三氟甲基）苯基]硼酸盐，的Boc =叔丁氧羰基） 。该反应提供了制备具有优异对映选择性的旋光杂环酸的有效方法。
• 吡咯酰胺类化合物及其制备方法与用途
  申请人：成都先导药物开发有限公司

  公开号：CN105732459B

  公开（公告）日：2019-05-31

  本发明公开了一种Ⅰ所示的吡咯酰胺类化合物或其药学上可接受的盐、晶型、水合物或溶剂合物：其中，R1选自氢、羟基、氰基、卤素、羧基等；R2、R3分别或同时选自氢、羟基、氰基、卤素、羧基、C1～C6的烷基等；R4选自羟基、巯基、氨基取代的苯基或环氧酮基团。本发明提供的式Ⅰ所示的新化合物，表现出了良好的去乙酰化酶抑制活性，具有预防和/或治疗由组蛋白去乙酰化酶活性异常所导致疾病的潜力；同时，本发明新化合物对不同的肝癌细胞具有良好的抑制活性，具有临床应用的前景。
• Bicyclic Pyrrolidines for Medicinal Chemistry via [3 + 2]-Cycloaddition
  作者：Vladimir I. Savych、Vladimir L. Mykhalchuk、Pavlo V. Melnychuk、Andrii O. Isakov、Taras Savchuk、Vadim M. Timoshenko、Sergiy A. Siry、Sergiy O. Pavlenko、Dmytro V. Kovalenko、Oleksandr V. Hryshchuk、Vitalii A. Reznik、Bohdan A. Chalyk、Vladimir S. Yarmolchuk、Eduard B. Rusanov、Pavel K. Mykhailiuk

  DOI：10.1021/acs.joc.1c01327

  日期：2021.10.1

  A general approach to bicyclic fused pyrrolidines via [3 + 2]-cycloaddition between nonstabilized azomethyne ylide and endocyclic electron-deficient alkenes was elaborated. “Push–pull” alkenes and CF3-alkenes did not react with the azomethyne ylide under the previously reported conditions, and we developed a superior protocol (LiF, 140 °C, no solvent). Among obtained products were medchem-relevant

  详细阐述了通过不稳定的偶氮甲炔叶立德和环内缺电子烯烃之间的 [3 + 2]-环加成来制备双环稠合吡咯烷的一般方法。在先前报道的条件下，“推拉”烯烃和 CF 3 -烯烃不与偶氮甲炔叶立德反应，我们开发了一种优越的方案（LiF，140 °C，无溶剂）。获得的产品包括与医药相关的双环砜、单氟、二氟和三氟甲基取代的吡咯烷。这种方法不仅允许制备新分子，而且显着简化了现有分子（例如，sofnicline）的合成。
• 3-AMINOETHYL-N-AMIDINO-2,5-DIHYDROPYRROLE DERIVATIVES HAVING ARGININE MIMETIC PROPERTIES
  申请人：——

  公开号：US20020026034A1

  公开（公告）日：2002-02-28

  1 The present invention ocncerns new amidinopyrroline derivatives of formula (I) with the meanings of the symbols as given in the description as well as a process for their production and their use in pharmaceutical preparations.

  本发明涉及新的式（I）的胍基吡咯烷衍生物，其中符号的含义如描述中所示，以及它们的生产过程和在制药制剂中的应用。
• Beta-amino acids
  申请人：Gellman H. Samuel

  公开号：US20070123709A1

  公开（公告）日：2007-05-31

  Disclosed are β-amino acid monomers containing cylcoalkyl, cycloalkenyl, and heterocylic substituents which encompass the α and β carbons of the peptide backbone and β-polypeptides made from such monomers. Method of generating combinatorial libraries of polypeptides containing the β-peptide residues and libraries formed thereby are disclosed.

  本发明涉及包含环烷基、环烯基和杂环取代基的β-氨基酸单体，其包括肽骨架的α和β碳，以及由这样的单体制成的β-多肽。还公开了生成含β-肽残基的多肽组合库的方法以及由此形成的库。